An operationally simple and fully regiocontrolled formal total synthesis of the montanine-type Amaryllidaceae alkaloid (±)-pancracine

被引：21

作者：

Banwell, MG ^{[1
]}

Edwards, AJ ^{[1
]}

Jolliffe, KA ^{[1
]}

Kemmler, M ^{[1
]}

机构：

[1] Australian Natl Univ, Res Sch Chem, Inst Adv Studies, Canberra, ACT 0200, Australia

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 2001年 / 12期

关键词：

D O I：

10.1039/b102252k

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Reaction of beta- nitrostyrene 4 with cyclohexane-1,3-dione (5) in the presence of DBU affords the Michael-addition product 6, which is readily elaborated, using straightforward chemistry, to the 5,11-methanomorphanthridine 2, acquisition of which constitutes a formal total synthesis of the racemic modification of the montanine alkaloid pancracine (1).

引用

页码：1345 / 1348

页数：4

共 21 条

[11] FULLY REGIOCONTROLLED SYNTHESIS OF DEACETAMIDOISOCOLCHICINE - FORMAL TOTAL SYNTHESIS OF COLCHICINE
BANWELL, MG
LAMBERT, JN
CORBETT, M
GREENWOOD, RJ
GULBIS, JM
MACKAY, MF
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1992, (11): : 1415 - 1426
[12] TOTAL SYNTHESIS OF MONTANINE-TYPE AMARYLLIDACEAE ALKALOIDS, WHICH POSSESS A 5,11-METHANOMORPHANTHRIDINE RING-SYSTEM, THROUGH CYCLIZATION WITH SODIUM BIS(2-METHOXYETHOXY)ALUMINUM HYDRIDE - THE 1ST STEREOSELECTIVE TOTAL SYNTHESES OF (+/-)-MONTANINE, (+/-)-COCCININE, (+/-)-O-ACETYLMONTANINE, (+/-)-PANCRACINE, AND (+/-)-BRUNSVIGINE
ISHIZAKI, M
HOSHINO, O
IITAKA, Y
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (26): : 7285 - 7295
[13] Synthetic application of pericyclic imino ene reactions of allenylsilanes enantioselective total synthesis of montanine-type alkaloids
Jin, J
Weinreb, SM
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1996, 212 : 47 - ORGN
[14] THE 1ST TOTAL SYNTHESIS OF AMARYLLIDACEAE ALKALOIDS OF THE 5,11-METHANOMORPHANTHRIDINE TYPE - AN EFFICIENT TOTAL SYNTHESIS OF (+/-)-PANCRACINE
OVERMAN, LE
SHIM, J
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1991, 202 : 7 - ORGN
[15] SYNTHESIS APPLICATIONS OF CATIONIC AZA-COPE REARRANGEMENTS .25. TOTAL SYNTHESIS OF AMARYLLIDACEAE ALKALOIDS OF THE 5,11-METHANOMORPHANTHRIDINE TYPE - EFFICIENT TOTAL SYNTHESES OF (-)-PANCRACINE AND (+/-)-PANCRACINE
OVERMAN, LE
SHIM, J
JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (17): : 4662 - 4672
[16] A STEREOSELECTIVE SYNTHESIS OF A BASIC SKELETON OF AMARYLLIDACEAE MONTANINE-TYPE ALKALOIDS, (+/-)-4A,11A-CIS-11,11A-SYN-5,11-METHANOMORPHANTHRIDINE RING-SYSTEM
HOSHINO, O
ISHIZAKI, M
CHEMISTRY LETTERS, 1990, (10) : 1817 - 1820
[17] SYNTHESIS APPLICATIONS OF CATIONIC AZA-COPE REARRANGEMENTS .23. 1ST TOTAL SYNTHESIS OF AMARYLLIDACEAE ALKALOIDS OF THE 5,11-METHANOMORPHANTHRIDINE TYPE - AN EFFICIENT TOTAL SYNTHESIS OF (+/-)-PANCRACINE
OVERMAN, LE
SHIM, J
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (17): : 5005 - 5007
[18] APPROACHES TO THE TOTAL SYNTHESIS OF MONTANINE-TYPE ALKALOIDS - A 1ST SYNTHESIS OF (+/-)-4A,11A-CIS-11,11A-ANTI-5,11-METHANOMORPHANTHRIDINE AND ITS TRANS-ISOMER
HOSHINO, O
ISHIZAKI, M
SAITO, K
YUMOTO, K
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1990, (05) : 420 - 421
[19] Total Synthesis of the Lycorenine-Type Amaryllidaceae Alkaloid (±)-Clivonine via a Biomimetic Ring-Switch from a Lycorine-Type Progenitor
Manas, Caries Giro
Paddock, Victoria L.
Bochet, Christian G.
Spivey, Alan C.
White, Andrew J. P.
Mann, Inderjit
Oppolzer, Wolfgang
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (14) : 5176 - 5178
[20] Acid-induced Favorskii-type Reaction: Regiocontrolled Elimination of Acyloin Mesylates Leading to α,β-Unsaturated Ketones and Application to Formal Total Synthesis of (R)-Muscone from Racemic Muscone
Ashida, Yuichiro
Tanaka, Akihiro
Hosomi, Kohei
Nakamura, Atsushi
Misaki, Tomonori
Nakatsuji, Hidefumi
Tanabe, Yoo
CHEMISTRYSELECT, 2016, 1 (12): : 3215 - 3218

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